1-methyl-2-(5'-methyl-2'-thienyl)benzimidazole | 78706-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-methyl-2-(5'-methyl-2'-thienyl)benzimidazole
• 英文别名: 1-methyl-2-(5-methylthiophen-2-yl)-1H-benzimidazole；1-methyl-2-(5-methylthiophen-2-yl)benzimidazole
• CAS: 78706-14-6
• 化学式: C₁₃H₁₂N₂S
• 分子量: 228.318
• InChiKey: ICVKRCRHESOEJM-UHFFFAOYSA-N

物化性质

• 熔点：
  75-76 °C(Solv: ethanol (64-17-5))
• 沸点：
  408.1±47.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-2-(5'-methyl-2'-thienyl)benzimidazole 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 1-methyl-2-(5'-formyl-2'-thienyl)benzimidazole
  参考文献：
  名称：

  Oxidation products of fused 2-hetarylimidazole derivatives

  摘要：

  Oxidation of 5-(1-methyl-1H-benzimidazol-2-yl)thiophene-, and -selenophene-2-carbaldehydes with potassium dichromate in 20% aqueous sulfuric acid afforded the corresponding carboxylic acids. Analogous reaction with 5-(1-methyl-1H-benzimidazol-2-yl)furan-2-carbaldehyde led to the formation of 1-methyl-1H-benzimidazole as a result of decarboxylation of the primary oxidation product and subsequent decomposition of the furan ring. Probable factors responsible for instability of 5-(1H-benzimidazol-2-yl)-hetarene-2-carboxylic acids were considered. The oxidation of 2-furylnaphtho[2,3-d]- and 2-hetarylphenanthro-[9,10-d]imidazoles gave, respectively, an anthraquinone analog and 6,7-quinones. pi-Electron-rich heterocycles in 2-furyl- and 2-pyrrolylphenanthro[9,10-d]imidazoles were oxidized completely, being replaced by hydrogen.

  DOI：

  10.1134/s1070363211080226
• 作为产物：
  描述：

  2-(5'-methyl-2'-thienyl)benzimidazole 以100%的产率得到
  参考文献：
  名称：

  ELCHANIPOV M. M.; SIMONOV A. M.; KOSENKO V. P.; OLEJNIKOVA L. YA., XIMIYA GETEROTSIKL. SOEDIN., 1981, HO 4, 520-523

  摘要：

  DOI：

文献信息

• Design and Syntheses of Palladium Complexes of NNN/CNN Pincer Ligands: Catalyst for Cross Dehydrogenative Coupling Reaction of Heteroarenes
  作者：Vikki N. Shinde、Nattamai Bhuvanesh、Anil Kumar、Hemant Joshi

  DOI：10.1021/acs.organomet.9b00695

  日期：2020.1.27

  of palladium(II) pincer complexes having NNN and CNN coordination modes. The new complexes were fully characterized with the help of 1H and 13C1H} NMR, HRMS, and IR spectroscopy. The structure and bonding modes of complexes were further authenticated with the help of single-crystal X-ray diffraction. Thermally robust and moisture-/air-insensitive palladium pincer complexes C1–C4 have been used as

  该报告描述了具有NNN和CNN配位模式的新型钯（II）钳形配合物的简单合成。借助1 H和13 C 1 H} NMR，HRMS和IR光谱对新配合物进行了全面表征。借助单晶X射线衍射进一步验证了配合物的结构和键合模式。具有热稳定性且对湿气/空气不敏感的钯夹钳复合物C1 - C4已被用作两个杂芳烃的交叉脱氢偶联（CDC）反应的催化剂，发现非常有效。该催化剂仅用1.0 mol％的催化剂即可成功活化包括苯并咪唑，咪唑，苯并噻唑，咪唑并吡啶，噻吩和呋喃在内的多种杂芳烃的C–H键，仅偶联剂的收率就很高。该催化剂对CHO，COMe，COOMe，COOEt，CONHPh，Me，CN，Br和Cl等官能团具有极好的耐受性。此外，该催化剂可重复使用多达四个反应周期，而效率仅有很小的损失。通过控制实验研究了CDC反应的机理，已表明NNN钳形配体（C5）的乙酸钯类似物是活性催化剂。
• Halo-Bridged Abnormal NHC Palladium(II) Dimer for Catalytic Dehydrogenative Cross-Coupling Reactions of Heteroarenes
  作者：Sreejyothi P、Samaresh Chandra Sau、Pavan K. Vardhanapu、Swadhin K. Mandal

  DOI：10.1021/acs.joc.8b01053

  日期：2018.8.17

  This work describes the dehydrogenative coupling of heteroarenes using a dimeric halo-bridged palladium(II) catalyst bearing an abnormal NHC (aNHC) backbone. The catalyst can successfully activate the C–H bond of a wide range of heteroarenes, which include benzothiazole, benzoxazole, thiophene, furan, and N-methylbenzimidazole. Further, it exhibited good activity for heteroarenes bearing various functional

  这项工作描述了使用二聚卤代桥联钯（II）催化剂轴承的异常NHC（杂芳烃的脱氢偶联一个NHC）主链。该催化剂可以成功活化多种杂芳烃的CH键，包括杂苯并噻唑，苯并恶唑，噻吩，呋喃和N-甲基苯并咪唑。此外，它对于带有各种官能团如CN，CHO，Me，OMe，OAc和Cl的杂芳烃表现出良好的活性。此外，我们通过进行化学计量反应中分离的活性催化剂和表征其作为乙酸根桥联（二聚一个由单晶X射线研究NHC）PdOAc。
• Synthesis of aldehydes and ketones of 1-methyl-2-(5-methyl-2-hetaryl)-1H-benzimidazole series
  作者：M. M. El’chaninov、A. A. Aleksandrov、I. M. El’chaninov

  DOI：10.1134/s107036321504012x

  日期：2015.4

  1-Methyl-2-(5-methyl-2-furyl)-1H- and 1-methyl-2-(5-methyl-2-thienyl)-1H-benzimidazoles were synthesized by Weidenhagen reaction followed by N-methylation. The obtained 1H-benzimidazoles were formylated with hexamethylenetetramine in polyphosphoric acid and acylated with carboxylic acids in polyphosphoric acid.
• Research on the chemistry of 2-hetarylbenzimidazoles. 4. Oxidation of 1-methyl-2-(5?-methyl-2?-hetaryl)benzimidazoles
  作者：M. M. El'chaninov、A. M. Simonov、B. Ya. Simkin

  DOI：10.1007/bf00506590

  日期：1982.8
• ELCHANINOV, M. M.;SIMONOV, A. M.;SIMKIN, B. YA., XIMIYA GETEROTSIKL. SOEDIN., 1982, N 8, 1089-1091
  作者：ELCHANINOV, M. M.、SIMONOV, A. M.、SIMKIN, B. YA.

  DOI：——

  日期：——